- Chiral (OC)Ru(salen)-catalyzed tandem sulfimidation and [2,3]sigmatropic rearrangement: Asymmetric C-N bond formation
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Asymmetric C-N bond formation was achieved in a highly enantioselective manner by using (OC)Ru(salen)-catalyzed sulfimidation and the subsequent [2,3]sigmatropic rearrangement: treatment of allyl aryl sulfides with p-toluenesulfonyl azide in the presence of a catalytic amount of (OC)Ru(salen) followed by hydrolysis of the resulting N-allyl-N-arylthio toluenesulfonamides provided N-allyl toluenesulfonamides of high enantiomeric excess.
- Murakami, Masakazu,Katsuki, Tsutomu
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- Synthesis and reactions of organic compounds with a nitrogen atom. Part XVII. Reactions of acyclic and monocyclic chlorides with phenyltelluro- and phenylselenosodium
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The reaction of neryl (3), geranyl (4), (+)-carvotanacetyl (5), (-)-carvyl (6) and perillyl (7) chlorides with phenylseleno-(1) or phenyltellurosodium (2), and then with chloramine-T afforded α,β-unsaturated toluenesulfonamides 8-11, which were reduced with sodium in liquid ammonia to allylic amines 12-15. Allylic phenyltellurides were oxidized by air to carbonyl compounds 29-31 or alcohol 28.
- Bakowska-Janiszewska,Scianowski,Uzarewicz
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p. 649 - 656
(2007/10/03)
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- Allylic amine formation by imination of allylic tellurides
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The imination of allylic phenyl tellurides with [N-(p-toluenesulfonyl)imino]phenyliodinane or chloramine-T affords the corresponding allylic amines via [2,3]sigmatropic rearrangement of the tellurimide intermediates in high yields. Application to chiral cinnamyl 2-(1-dimethylaminoethyl)ferrocenyl telluride results in the formation of the corresponding chiral allylic amine, 3-phenyl-3-tosylaminopropene, with 93% ee.
- Nishibayashi, Yoshiaki
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p. 6725 - 6728
(2007/10/02)
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